Organic Chemistry- SN2, SN1, E2, E1 Mechanisms

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Acetone

aprotic

acetonitrile (with n and triple bond)

aprotic

DMF

aprotic

DMSO (sulfur d. bonded to oxygen)

aprotic

HMPA

aprotic

Nitromethane

aprotic

CH3OH

protic

H20

protic

HCONH2

protic

HCONHCH3

protic

Cl-

good nucleophile, good leaving group

Br-

good nucleophile, good leaving group

I-

good nucleophile, good leaving group

H20

weak nucleophile, good leaving group

OH-

good nucleophile, basic, BAD leaving group

HS-

good nucleophile only

H2S

good nucleophile,

CH3CH2O- (EtO-)

good nucleophile, good base, poor leaving group

(CH3)3O-

good nucleophile. good base, poor leaving group

NH2-

good nucleophile, good base, poor leaving group

RS-

good nucleophile only

RSH

good nucleophile

CH3CH2OH

weak nucleophile, weak base

CH3OH

weak nucleophile, weak base

F-

weak nucleophile, poor leaving group

R2N-

good nucleophile, basic

RO-

good nucleophile, basic

LDA

sterically hindered base E2

t-BuOK

sterically hindered base E2

RCOO-

good nucleophile

N3-

good nucleophile

N triple bond C

good nucleophile

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